Tom Osborne, two ex-Microsoft execs and an astronaut walk into a bar…

Doug Burgum (left), was among the friends and colleagues to roast Jeff Raikes, an Ashland, Neb. native and the CEO of the Bill and Melinda Gates Foundation, on Thursday night in Omaha.

Today, one of the men delivered the keynote speech at an event hosted by the school named after the other man. And, for the most part, Doug Burgum and Jeff Raikes conducted themselves with the sort of decorum expected of a couple of former high-ranking Microsoft executives.

But on Thursday night, Burgum and Raikes more closely resembled the computer kings of comedy.

Around these parts, Raikes is often cast as the quintessential local boy done good. The Ashland, Neb. native enjoyed a successful career as a software exec and now serves as CEO of the BIll and Melinda Gates Foundation. But he’s still a Husker at heart, known for his support of both his home state’s favorite collegiate football team and that school’s computer science and management program.

Of course, the sort of success Raikes has achieved often is accompanied by people with an overwhelming desire to pay tribute. And if comedic evisceration isn’t the sincerest form of flattery, well, it’s at least the most entertaining one.

That’s where Burgum comes into play. Before delivering a talk today at the Raikes School, Burgum was part of a team charged with the task of roasting Raikes on Thursday night at the Omaha Press Club, where Raikes became the Club’s 133rd “Face on the Barroom Floor.” Burgum, the former CEO and chairman of Great Plains Software and a former senior VP at Microsoft, was joined by Tom Osborne, the University of Nebraska athletic director, Clayton Anderson, a NASA astronaut, David Graff, the CEO of Hudl, and Mary Fricke Bohn, a senior VP of the Farmers and Merchants Bank of Ashland.

(Left: A caricature of Raikes by artist Jim Horan was unveiled at Thursday night’s roast.)

Now, Silicon Prairie News frequently covers the Raikes School, and we catch up with Raikes himself as often as possible when he returns to the area. In that coverage of Raikes, we tend to provide a charitable view of the man and his work. But on Thursday, Raikes‘ roasters took the rose-colored glasses through which he’s so often seen and smashed them to smithereenes.

Growing up in Ashland, Bohn knew Raikes as the schoolmate with the way-too-tight jeans and the “irritating” style as a percussionist in the school band. Raikes also quickly established himself as someone whose passion for sports consistently outpaced his athletic ability.

“He’s not very big,” Osborne said of the scouting report on Raikes, “but he sure is slow.”

Burgum recalled the the story of Raikes receiving his first athletic letter. “He got his first athletic letter when he was only a high school freshman,” Burgum said. “It came from the coach. It read: ‘Dear Jeff, please don’t come out next year.’ “

Just about all the roasters teed off on Raikes’ golf game. “He was primarily known as a short hitter,” Osborne said. “A good drive for Jeff was about 100 yards.”

Added Burgum: “He does have this beautiful short game. It’s too bad the only place he uses it is off the tee.”

Despite those shortcomings, Osborne said, Raikes enjoyed his fair share of success on the links: “He still won, and he won an amazing number of times. Nobody could figure it out … but actually what he did is he talked his opponents to death. He never shut up.”

That mile-a-minute mouth served Raikes well off away from golf, too, according to Burgum. “He graduated with honors,” he said. “Magna cum loudest.”

“What he did is he talked his opponents to death. He never shut up.” – Tom Osborne, on Jeff Raikes’ secret to golf success

But Raikes‘ skill as a listener never quite matched his ability as a talker, Osborne said. And that’s what led Raikes to Microsoft. When Raikes worked at Apple, Steve Jobs told him not to join Bill Gates’ company, because it was bound to go belly up soon. But, Osborne said, “He didn’t listen to coaching.”

Fortunately, Raikes found himself well-suited for life at Microsoft and began contributing almost immediately. Recalled Anderson: “Some of his greatest early insights at Microsoft included, ‘I agree, Mr. Gates … can I get you some coffee, Mr. Gates?’ ”

Raikes was so enthusiastic about his longtime employer that students once speculated the school that now bears his name might be given another moniker. “In all honesty,” Graff said, “we should just have been happy that it wasn’t the Microsoft Windows 2010 Honors Program for Computer Science and Management, Ultimate College Edition.”

Burgum said that if Warren Buffett — who attended the roast — is the Oracle of Omaha, then Raikes is unquestionably the Wizard of Wahoo (another Nebraska town a stone’s throw from Ashland). Eventually, Buffett got in on the fun. In a video segment played during the roast, Burgum asked Buffett about Raikes‘ chops as an investor. “He’s got a nice smile,” Buffett said, “but I’m not sure how much he’s really got upstairs.”

Raikes flashed that smile often throughout the night, taking the revisionist account of his life story in stride before dishing out a few barbs of his own. But for all the besmirching of Raikes’ name, the Windows man came away from the event, somehow, looking squeaky clean.

“He’s certainly an asset not just to Nebraska, not just to Seattle, but the world,” Osborne said. “And so I’m proud to be able to call him a friend.”

Added Burgum: “Jeff, for all you do, and for all the lives you touch, we say thank you, for being the Wizard of Wahoo.”